


Babysitting Bonnie

by BizarreJoe



Category: Toy Story (Movies)
Genre: Babysitting, Bathing/Washing, F/M, Her mom approves, Oral Sex, Sex, Vaginal Sex
Language: English
Status: Completed
Published: 2020-03-20
Updated: 2021-01-02
Packaged: 2021-02-28 21:16:00
Rating: Explicit
Warnings: Underage
Chapters: 2
Words: 16,826
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23223886
Author URL: https://archiveofourown.org/users/BizarreJoe/pseuds/BizarreJoe
Summary: Mrs. Anderson asks Andy to babysity Bonnie while she is out of state for the weekend. Andy finds babysitting easy, way too easy.
Relationships: Andy Davis/Bonnie Anderson
Comments: 16
Kudos: 48





	1. Babysitting Alone

**Author's Note:**

> This story was requested by someone who wishes to remain anonymous. If you want one contact me through discord.

Andy Davis didn't like to admit it, but college life was chewing him up. Of course, that wasn't exclusive to him, everyone was dealt a bad hand in college, but for the boy from the suburbs who hadn’t really been challenged all that much in the past, it was turning his brain into paste. Maybe that was the reason, maybe that's why he decided that instead of a week of partying or any of that wild white nonsense, he would instead go back home and spend the entirety of his spring break napping at his mother’s house. Anyone in the dorm could consider it lame if they wanted to, but he considered it healing, because after four whole days of being lazy around the house, he was sure nothing could top how well he felt at the time. 

The schedule for his first day back at home was simple, sit on the couch with a bag of sour cream & onion Ruffles and watch some dude on the history channel talk for hours on end about how every single man made marvel or human achievement in history was actually made by aliens. It wasn’t exactly convincing, but it was fun, and there was nothing on TV quite like it, so nothing was going to move him from his spot. 

Or that's what he thought, because right as the 4th episode of this marathon was about to start, someone rang the doorbell. He groaned and rolled his eyes because his mom was at the store so he knew that he had to be the one to go and open the door. After exhaling a breath of frustration, he decided to simply get it over with. 

He walked to and opened the door and was surprised to find Mrs. Anderson. The nice lady from a few houses from down the block, he stopped frowning immediately. Mrs. Anderson was a nice lady, she worked in a Daycare, and had in fact babysat him way back when he was a kid. Even if she didn’t visit much, she was always a welcome sight. 

“Mrs. Anderson!” He said happily, “what brings you here?” 

“Oh, I was looking for your mother” She made a small pause before asking “Is she home?” 

“Actually, no” Andy said matter of factly, scratching the back of his head “But what did you want? I could call her or tell her when she comes home”

“You, you could do it yourself” She said, as if she got an idea “You’re a really responsible kid, aren’t you?” 

“I’ve been told that, yes” 

The lady let out a chuckle before continuing “Say Andy, would you like to earn a few dollars?”

“Sure” 

“Well I need to go away for a few days to finalize some papers for my new house… and to make sure that the moving company isn’t going to screw me over” 

“Wait… You’re moving away?” 

“Yes, and well, I was going to ask your mom if she could take care of Bonnie and keep an eye on the house while I was away, buuuuut, since you’re here, I'm going to ask you. Would you mind doing some babysitting and house sitting for the week?”

Still processing the fact that the nice lady that took care of him while he was a kid was going to leave the neighborhood, Andy blurted out “Yes, sure” before realizing what he had agreed to. 

With a “Great!” Anderson sealed the deal. They had a small, inconsequential conversation before the lady told him to come to her house by four pm so he could start. After that she just left and let him prepare. 

Once his mom and sister came home from the store. Andy explained what he had gotten into. Something his sister Molly mocked him for, but his mother trusted him enough to let him stay at the Anderson household for a few days, and along with her approval she gave him a few tips about how to take care of a child of Bonnie’s age. By 3:50, he was ready to go, he had a backpack with a few changes of clothes. It was when he actually made the trip that he realized that the baseball cap may have been a bit much, because he didn’t even get to sweat when he made the four house trip from his mother’s house to Mrs Anderson’s.

The conversation they had at the door was short, sweet and to the point, the woman let him in to greet her daughter again, and before the hour was up, she was gone and (as she made clear) she would return by the end of the weekend. Andy wasn’t exactly new to babysitting, he had taken care of his sister for years, and babysat a few kids over the years, but this was his first time actually having to do it for a whole weekend in the kid’s house. Still, he didn’t expect it to be that different at all. 

Which was where he was wrong. 

Bonnie was quite the active girl, and she knew the layout of the house quite well, unlike him, so the first hour he had alone with her was like playing an importu game of hide and seek while blindfolded. it was tiring… but it was for his benefit in the long run, because having decided that he was fun to be around, Bonnie trusted him more.

Taking care of her would be easier the more that she trusted him, and he knew the best way to get there, at least with a girl her age. Toys! He asked her about them, but she answered by saying that her mom had put them in a box that she shoved into her car a couple of days prior. Andy couldn’t avoid feeling disappointed by that information, not only because getting Bonnie to be quiet would take longer now, but also because even though he was too old for them now, the nostalgia of playing with his dolls was somewhat alluring to him. Still he’d have to deal with this by other methods.

Methods that, as the hours went by, he would realize were pretty freaking tiring. Bonnie was as energetic as she was creative and his tired brain made it difficult to keep up with her, so he decided that some good ol`time on the tv would help him to keep her in one place, they started with some cartoons, he sat her down on the sofa beside him and started to do some zapping through the channels to see what was good, he decided to stay on the Cartoon Channel, it had been years since he had sat down and watched something (Andy dropped off the channel by the time that they started showing real people shows in a Channel dedicated to cartoons) as of right then, they were showing a modern comedy reboot of an old action cartoon he used to watch waaaaay back when he was a kid. It was neon colored, loud, obnoxious and apparently it was entrancing for Bonnie, because she was looking at the screen dumbfounded for as long as it was on. After the third episode of it had ended and the channel geared to air another one, Andy got curious and looked up the channel’s schedule with his phone… And found that it was filled with this program, it was going to be on until the sun went down, take a break for two hours to show an avant garde show about a cat, then go back to the loud obnoxious reboot until the sun went up again. 

Andy let out a massive groan, the show was a drag, but the little girl seemed to love it so he remained with her on the sofa for hours on end. By the time he heard her yawning, he had lost track of how much time had passed since he zoned out, but a quick glance outside made it clear that the afternoon had already passed. Seeing that Bonnie was already sleepy he decided that it was a good moment to take her to her room and put her to sleep.. 

The girl didn’t really protest when he picked her up, instead closing her eyes and resting her head on his chest. He was sure she was already snoozing when he put her on her bed. If the rest of the weekend went like this, then this would be easy money. 

Yawning himself, he decided to get out of the room and go to the one he would be sleeping in, but he stopped himself once he caught his own smell while stretching his arms. Andy wasn’t sure when he sweated so much to get that smell, but he was sure he wasn’t going to sleep with it. So he went to Mrs. Anderson’s room to pick a towel, and made his way to the bathroom taking his clothes off and leaving them on the ground along the way, he knew he’d have to pick them up before morning but there wasn’t enough cells in his body that cared at the moment, instead he just focused on getting in the shower, closing the very transparent crystal door to it and just letting the warm water come down on him . 

He just turned the knob and the lukewarm water hit him. He had his eyes closed, trying to relax and focus on cleaning himself, Andy gave a sigh and adjusted himself to let the shower hit his back giving him an almost therapeutic massage on his weary neck and shoulders, as he opened his eyes and thought about the embarrassing mess he left with his dirty clothes all over the wooden floor, he mentally followed each garment from nearest to farthest until he noticed that he could see the last piece of his clothing (his underwear) though the small gap in the door.

Deciding that he would just pick them up when he was done, Andy merely closed his eyes and started caressing his body, washing it with water and a handful of soap, it was a quite relaxing experience…And he knew how to top it off. 

With the help of the soap, he started rubbing his own member. For the first few minutes it was weirdly intense, maybe because he hadn’t done it a lot since he went to college but he didn’t want to stop, he started picking up speed so quickly that he started to move and groan, and letting out a moan when he found that he was against the wall. He opened his eyes and saw, the lack of a visual aid didn’t make it any less of a powerfully pleasurable experience. He slowed down his wanking to avoid chafing and it was at that moment that he noticed something at the door, a small green eye could be seen peeking from the ajar the door, with its owner hiding in the shadows behind it.

There were only two people at home right now, so at this point any normal person would stop and reprimand the child, but maybe because of the months of abstinence, Andy had a perverse thought, instead of even acknowledging that she was there, he made his self pleasure into a spectacle. Showing the curious girl the first erotic show of her life. He slowed his pumps to a crawl and used the palm of his other hand to rub his cockhead, on it’s own it was exhilarating, but knowing that there was someone watching (that shouldn’t be at all) made it all the more intoxicating. The build up to his climax was the most delicious agony that he had ever experienced in his entire life, every pump brought him closer and closer to a feeling so heavenly that when he finally came he ended up sliding down the wall and sitting on the floor for who knows how long. 

Andy heard the very recognizable sounds of someone running on a wooden floor, he thought that she probably ran after seeing him shoot rope after rope of cum against the glass walls of the shower. He thought that he would have probably done the same thing if he had seen some dude do what he did.

He let out a tired chuckle, the girl was too curious for her own good, at least at this age, he thought as he turned off the shower. After a few minutes of recovering his energy, he went back into Mrs Anderson’s room to finish drying up and catch some much needed shut eye.

Anyone with any common sense would have been terrified of what could happen, what that girl could do or say, she could fully destroy his life, but Andy was a tired, yet very satisfied young man, all he wanted to do now was to rest and worry about other stuff tomorrow, Bonnie was young, she would probably forget about what she saw.

Andy did not dream, but he still ended up having the most restful night of sleep that he may have ever had.

Even if it preceded the wildest and most memorable day in Andy's life, the next morning was remarkably normal, he awoke early in the morning, even the binders didn't help much against how intense the sun was outside the window. The day prior he may have cursed the world for making him wake up so early, but this was a new day and he was in a great mood and full of energy. He dressed himself and went to the kitchen to make himself and his diminutive voyeur some breakfast. He barely knew her so he didn't know what she liked, but you can't go wrong with cereal, if kids and college students had something in common was their undying love of cereal. 

He went above and beyond mixing and matching cereals for his enjoyment, and doing the same for her (just to be fair). He wondered if he would have to wait for her for long. Back in the day he used to wake up early on Saturdays to watch cartoons. But he didn't know if kids still did that, which made him feel old. 

Andy went to her room to check on her, and found her dressed in her pajamas, getting out of bed and putting her pink slippers on. She was groggy and yawning but she was adorable nonetheless. 

She greeted him when she saw him and he told her that breakfast was ready, her face instantly lit up. She was excited when he picked her up and took her to the kitchen. He sat her on a chair and put the sugary abomination in front of her before adding in her milk. He ate as he saw her devour her food. He was instantly able to see why she was so pudgy. 

Before long she had eaten all of it while he was still halfway through his. He asked "do you want more?"

"Can I? Mama always says that I can't have too much"

"She may, but your mom isn't here is she?"

"No" she said, kinda sad for a moment. 

"She won't be back until monday, so for two days, we can do whatever we want to"

"Anything?"

"Anything you want"

She looked at her bowl for a second before looking up at him and saying “More!”. He poured bits and pieces of three different cereals into her bowl, before adding milk to it. Bonnie saw the milk coming down with so much attention, as if it was hypnotizing her, in her trance, she couldn't avoid asking. "Mr. Andy, do boys make milk too?"

Shocked, Andy felt as if he had his balls trying to come out of his throat, he didn't know what to say, but he knew how kids were, that girl wasn't going to stop asking until she got an answer, so he said "Ehhh, what do you mean?" To try and stall her. 

With complete honesty, she answered "Last night, you left the door open and I saw you shoot something white from your peepee"

"Well…" he said, before being interrupted.

"Mama says that only moms and cows make milk, what was that?”

Andy realized what he had in front of him, a girl who knew nothing about the birds and the bees, a completely innocent creature. His common sense told him to pull back, to let last night be last night and explain just enough for her to be satisfied and just go back to being safely normal… but the tightness that was growing in his pants was stronger than that, he wasn’t even worried about the abnormality of these impulses, he just smirked, before answering.

“Well, you see, we do make milk, it's just harder to get!” 

“Wha? Why?!” 

“Because we have to be milked” He said with a mischievous smile in his face. 

“You were milking yourself last night?” 

“Yes” 

“Why?” 

“Because it feels real good” 

“Does it taste good?” 

“I don’t really know… Do you wanna find out?”

The girl nodded excitedly before asking if she “was going to see his thingie”, he answered by saying that she was going to be doing more than seeing it. He saw her go from doubt to wonder in less than 5 seconds, she asked if she was going to have to milk it, when Andy answered with a positive nod, she clapped. Andy pulled her down from her high chair and told her to follow him as he took her bowl and brought it to the living room and put it on the coffee table. He explained that it was going to be too uncomfortable to do it where she was before.

With wonder and excitement she saw as he pulled down his zipper to reveal his half hard erection. It was like nothing she had seen before, it was as long as her arm and just as thick as her arm too.

The girl found that it was warm, it was hard and when she took it in her hands she realized that it was heavy. With a smile on his face he explained what she needed to do, once he was done explaining, he just rested on the sofa and just let her do her thing. And that she did, she approached jacking him off as she approached any new experiences, with excitement and curiosity and above all, energy. 

It wasn’t the best handie that he had ever gotten, but it was the most exhilarating. It was so wrong, but he didn’t want it to stop at all, the sheer perversion of it brought him closer to his orgasm, he had a kid who was  _ barely _ half the age of his own little sister handling his cock, and it felt so furiously intoxicating, it didn’t take long for him to start leaking precum. 

Something that Bonnie immediately took interest in. She stopped moving for a second and paid close attention to the small, transparent droplets that were coming out of his dick. Instead of wasting any time on wondering, Bonnie asked “Is this pee? Did i make you Pee?”, Andie didn’t know if it was her big green eyes, or the undeniable innocence in her words, but what she said made him snort back a laugh.

“No, its nothing like that” He said, the humor of the situation helping him normalize it somehow “It just means the milk is right about to come out”

A spark of excitement flared in her eyes and she went back to jacking him off with gusto, she went faster and faster, as fast as she could manage. Andy bit his lower lip, feeling his balls tighten with each motion, his orgasm built to an unbearable peak. Once it was imminent, he quickly picked up her bowl from the coffee table and told her to stop and watch as he put the bowl close to his dick. He gave himself a few more pumps before he started to shoot rope after rope after rope of thick, pearly white cum on her cereal. It mixed seamlessly with the milk below giving it an appearance similar to a bowl of cereal with some condensed milk on top. He thought that he would have shot more cum if he hadn’t jerked off in the bathroom on the night prior, but a single look at Bonnie proved that nobody in the room was really disappointed with it. 

The girl looked at her food as if she had discovered something amazing and new, and in a way, she had. It looked like condensed milk on top of her cereal, and in her mind, thats exactly what it was. “Can I eat it now?” She asked, her voice was filled with childish impatience and anticipation. 

“Of course” Answered Andy with a smile, before adding “eat it while its warm”

The dug into her food like a hungry animal, eating spoonfuls of the cum stained cereal, barely even stopping for breath before shoving the next one into her mouth. It was then that Andy realized something, something very important. Bonnie truly didn’t know anything at all about this. 

“Your milk tastes salty” said the little girl, bringing the zoned out teenager back to reality. 

“Did you like it though?” He asked, realizing that she had finished the bowl while he was lost in thought, a bit worried that she may have hated the experience.

“I love it! Your condensed milk is salty and sweet and delicious” She said happily.

“Thats because it is natural” He excused, tried to hide a little that he said it as a stealth question from his the little girl. 

Bonnie looked confused, but accepted the explanation before asking “Can I have more?” She asked, extending her bowl towards him without even a hint of irony or disgust, making all kinds of wild thoughts go through Andy’s mind.

“Maybe later.” He told her, making a small pause to think about what to say, before just telling her truth “I can’t do it all the time, i need to recharge for a long bit before I can shoot that much again” 

“Oh” said the girl looking saddened. 

“I’ll tell you what, If you’re a good girl today, I’ll give you more for dinner” 

The speed with which her smile and energy came back to her almost gave Andy whiplash. “But at least she is excited for it” he thought. Andy told her to go play or watch cartoons before he sat down on the sofa behind him, he started to shove his penis back into his underwear, but before zipping up his pants, he realized something, Bonnie never had any kind of sexual interaction, or any kind of education about it. 

For a sick second, he wondered if he could get away with having her penis out in front of her through the day and pass it as normal. Before long, he was pulling his penis back out, and just letting it rest outside his pants to see how long it took her to notice.

After rummaging through the room for a bit, the girl came back with a childishly adorned tablet, she tapped away at it before it started to play what he assumed was a youtube video. She passed right in front of him, completely unphased by his member. To dissimulate his interest, he looked around for the TV’s controller before sitting on the floor right beside her when he got it. He turned the TV on and he started to zap around the channels, something that got Bonnie’s attention. 

She looked up at the changing channels before looking at him, and asking what he was looking for. He said nothing, and she went back to her tablet. He stopped at a network that showed older cartoons like the ones that he used to watch as a kid. They were showing Buzz Lightyear of Star Command, and he couldn’t avoid feeling a pang of nostalgia for it, he remembered losing entire hours of his Saturdays watching the show on VHS. He didn’t manage to notice that the same had happened while he was watching it up until the show ended and the credits rolled.

“That was so ama-zing!” 

He looked to his side, he was so focused on the show that he didn’t realize that she put down her tablet and watched along with him. For more than a long while, they talked about it, Andy told her about the adventures of Buzz, NX, Mira Nova and Booster as they tried to save the Federation from Zurg. The entire interaction was so relaxed and casual that he completely forgot that he had seven inches of dick outside of his pants. 

At least until Bonnie cocked her head looking at it, and said “are you going to keep your pee pee out?”

He didn’t have any time to think of a intelligent response, so, he simply went with “Yeah, it needs some air after getting milked” 

“Does it feel nice?” 

“What?” 

“Having your pee pee out!” 

“Oh yeah, it’s the best” He said, without thinking, out of sheer instinct, he continued with “You should try it too” 

Nobody in their right mind would believe that. But kids like Bonnie weren’t at an age where they had “right minds” so she nonchalantly stood up, took off her slippers, and dropped her pajama pants without any protest, and to Andy’s surprise, her underwear followed them immediately. 

He couldn’t even hear the metaphorical voice of his conscience telling him that this was wrong, it was all silent under the powerful impulse to keep pushing to see what else he could get away with. This was a once in a lifetime opportunity, and he wanted to do as much as he could. 

Whenever he remembered what happened that weekend, he couldn’t ever for the life of himself avoid thinking about how much he enjoyed that afternoon. The fact that she was basically a very joyful and very actively curious girl just made it easier for her to get into situations where he could see her little body in all of it’s splendor. 

He took off his pants and didn’t present it like a game, or something that adults did, but let her treat nudity as something comfortable, and fun without any pretense. Every flash that he got of her pussy or her ass it was because she was having fun or innocently playing around. Because she was having fun. 

He found that beautiful. 

Still, his body couldn’t understand the poetry of it, it just found it tiring to keep up with her childish antics through the day. He sweated up a storm and she did too, and while he loved how her sweaty little body looked like brown glistening caramel, by the time that the sun started to go down they were starting to smell. So he told her to get into the shower, they were going to take one before the house stank. 

  
He had been authoritative when he said that, yet, when the time came to actually get in the shower with her and closed the glass door, he felt suddenly intimidated, not by her, but by the situation. He had spent almost the whole day naked from the waist down with his penis near her face the whole time, and yet he never felt as nude as he felt when he entered the shower. 

Maybe it was the fact that he knew that she was expecting him to touch her to help her wash herself, or maybe it was that he knew that the situation still made him horny. Knowing that he couldn’t actually back out of that situation though, he, after some small attempt of conversation, told her to stand under the shower, as he took some soap and a bathing sponge and he started to clean her. He started by her shoulders and made his way down her body, part by part, arms, chest, waist, legs, he took special care of those. He would have been lying to himself if he didn’t admit that he was taking joy in it. Sure for her it was just her babysitting helping her clean her body as she applied her favorite bubble gum scented shampoo, but for him? He was taking the opportunity to touch and enjoy as much of her as he could. 

But then he got to her thighs, and that gave him pause. He had full access to her pussy like this, and she trusted him and liked him. Would he be able to take advantage of…

Before he could even finish wondering to himself, he had already dropped the bathing sponge, and was using his hand “to wash her” crotch. Bonnie let out a sharp “eeep” sound, at the surprising and strange contact. He was touching her vagina in a way in which neither her nor her mother had ever touched it before, and it was making her feel so… weird. Her body felt warmer, her mind felt fuzzier, and the longer he did what he was doing the more that her body seemed to react. Even if it was weird, it felt so good, it made her knees weak and her back felt like a soft current was going through it. Sensations that increased tenfold once Andy started touching that one nub above her slit, he massaged it like there was no tomorrow and her body and mind started to go crazy as a result. 

  
He didn’t know what he expected when he started doing it, he didn’t even know if girls of Bonnie’s age could even cum yet, but once she finally reached her climax, it was obvious that they could. Because as Bonnie moaned louder and louder, her body began to have small spasms and once they were over, even under all the water coming from the shower, Bonnie began to squirt a warm liquid from between her legs. Once it was done, she fell back towards the wall. She let herself slide down the wall, and sat on the ground letting the lukewarm water from the shower wash away whatever came out of her. Her legs felt like they were made of jelly, hell her whole body felt like that, and as Andy took his hand away, he smiled at her, as if he knew about the great feeling that he gave her. It took her a minute to realize, but he probably did. 

“That was Ama-izing!” She said, smiling from ear to ear. 

“I know” And said, coyly. 

  
The rest of their bathing session went almost normally, they did all the things her mother always did to her, but when it came time for him to wash himself, she insisted on letting him wash his parts. And after some hesitation, he left her. She used soap, and with his instructions, she did something really similar to the “milking” from that same morning. She was as energetic as she could and she couldn’t be any happier than when she saw that jet of white milk shoot out of it and stick to the wall behind her. 

Andy praised her and she felt like everything was right and good in the world. They finished their shower and he did his best to dry them both with the towels that were around the bathroom. Once she went looking for her underwear, he told her that it wasn’t necessary, that they didn’t have anything to hide from each other. So, she listened to him, after all, she had already seen her nude, and she had already seen him nude, so what he said made sense.

  
When they got out of the bathroom they realized that night had already fallen. After a quick dinner, it was time for bed. She was going to go to bed in her room, but she didn’t want to feel cold, so she turned around and asked Andy “Can I sleep with you tonight?” 

Andy smiled, picked her up, and brought her to bed with him. As much as he enjoyed the day and the possibilities of having this naked, trusting girl in bed with him, he was exhausted, so, getting her to actually sleep was the objective. So he picked a bedtime story from her room, and fortunately for him, by the middle point of it, they were both asleep.

The morning chirping of robins in the yard beckoned in the first rays of light between the drawn curtains of Bonnie’s mother’s room, the shadows casting across a pair of naked bodies lying on the queen bed in the centre of the room. It was there that Andy awoke, his naked form wrapped around the equally bare figure of Bonnie, the largest gap in a big and small spoon one might be able to find.

Stretching and yawning, it took a moment for Andy to recollect his memories of everything that had happened the previous day, though those were quick to recall once he looked down at the petite girl pressed up against him. Bonnie’s bare back was pressed squarely against his chest, letting him not only feel her soft, warm skin, but also her steady breaths as she soundly slept under his protection.

The young adult was lost to the time as he watched her for God only knows how long. Just watching her chest rise and fall with her breaths was enough to captivate him, her pert, dark nipples almost swaying in his mind, tempting him to act. He held back, but only to further absorb her peaceful and luscious body into his mind. Her soft things and welcoming pussy rested mere inches above his cock, already straining from morning wood.

It wasn’t long until she woke up as well, snuggling up closer to him, letting his dick slide between her plump thighs as she looked up into his eyes.

“Good morning, Andy!” She said, cheerfully, worming her way up towards his face, much to his dismay as his stiff member was released from her soft embrace.

“Morning to you too,” He said, softly, trying to hide his disappointment at losing that intimate touch on his eager member. He decided to take the next best thing; with her head drawn so closely to him, he couldn’t resist turning his head down and planting a kiss on her perfect lips.

Though she seemed surprised at the kiss, Bonnie didn’t think much of it. After all, her mommy gave her plenty, and, as her babysitter, Andy was essentially playing mommy for her while he was here. Instead, she decided to play along, though she couldn't quite tell how, these kisses seemed different from the ones her mommy gave her, but were still so much fun for her.

Kissing back up to him, her reach didn’t quite make it, leaving her lips pressed into his neck, though he seemed to appreciate the effort all the same as he arched his head back in satisfaction. The desire only grew in Andy as he felt her eagerness through her actions on him, forcing him to full her up and push his tongue into her mouth, fully embracing the little girl in his grasp.

Though shocked at Andy’s unusual assertiveness, the girl was more than happy to let his tongue explore her mouth, her own tongue twirling around his as he tongue fucked her mouth for what seemed like almost an hour but it was only a few minutes.

Eventually, the desire within Andy built up more than he could handle, his unencumbered cock twitching freely, yet touching only cool air, that frustration eventually broke within him. Grabbing Bonnie by the shoulders, Andy broke his kiss with her, “Alright, now let’s get you back down there,” pressing the girl down, she effortlessly slid across the mattress, until her cunt was aligned with his waiting cock.

He would have been lying if he said he wasn’t worried about what could happen once he pushed it in but he was too horny to think clearly. He told her that it was going to sting a bit, but that it was going to feel really really good later. She trusted that he wasn’t going to hurt her, so she nodded and let him do his thing. He sucked a bit of air before pushing himself inside of her. His mind implored him to panic once he saw small droplets of blood around his dick once he started to pull out, but he knew it was just her hymen breaking. 

He pushed back in again, and this time once he kissed her womb, he stayed still and told her to tell him when it was okay to start moving. She bit her lip for a while, she was trying to get used to the new, alien (yet not entirely uncomfortable) sensation. It was when it didn’t hurt as much -if at all- she nodded to let him know it was time. And what happened after was something that she would remember for the rest of his days.

When he started pumping it was so different. It was like the sensation she had in the bathroom the night before, but far, far stronger, exhilarating and intoxicating, her young mind couldn’t process the sensation as anything more than pure ecstasy. Every time he pulled out she felt empty, incomplete, and every time he pushed in she felt like she was going up to the heavens and coming back just to go further beyond.

Just like the night before, the feeling was making her body act weird, but this time in a completely different way, her back arched to accommodate him, and she had the instinctual desire to ask for more, and she did, multiple times, asking him louder and louder to make her feel even better. 

Andy was more than happy to accommodate, losing much of his restraint, not just because she asked for it, but how she asked for it. Her cries of ecstasy pushed Andy further than he had ever felt before. The way this young girl was moaning and begging like the most seasoned whores only encouraged him to go even harder, no longer trying to hold back for her own safety, it growing ever obvious that she could take it.

It wasn't long until his breathing became laboured and his humps erratic, his orgasm quickly approaching as the tight, spasming cunt he was buried in milked his cock better than any college girl he had hooked up with. With one final thrust, Andy's cock pushed in as deep as it could go, his head wrapped in her tight cervix, and finally released everything that has built up this morning.

Several ropes shot into her eagerly awaiting womb, which quickly filled with his seed before filling her cunt and beginning to leak out of her, Bonnie's tiny pussy unable to possibly handle the full load of an adult.

After several moments of catching their breath and calming from their respective highs, Andy pulled out of the child's twitching snatch, a steady stream of thick cum following behind.

"Alright, young lady, I think it's time for you to shower off and get ready for breakfast," Andy said, smiling to himself as the days itinerary ran though his perverted mind. Once he stood up, and gave her a minute to follow him, which wasn’t easy for a few minutes for no other reason than she feeling that her legs were made of jello. 

He offered to carry her to the bathroom, but she didn’t want him to, she wanted to walk. He let her not only because it was what she wanted, but also because she had a small trail of cum coming out of her and he loved seeing how it went down her leg. Before long, he was watching the drops fall to the ground straight from her pussy as they both walked to the bathroom and got in the shower, her mom would come back home during that same night and it would be better if bonnie wasn’t all sticky when she came back. 

It was too soon after sex, and didn’t want to shaff her so he didn’t try anything. But that doesn’t mean that nothing happened in that shower, as when he was halfway through it, she grabbed his dick unprompted, and started to lick it.

Even though he didn’t like seeing a gift horse in the mouth, he asked her what she was doing, he answered “I want to know how I taste”. 

He gave her back a smile and let her do her thing, only speaking when she was doing something wrong, and only to tell her how to do it better. It didn’t took long for her to do magic with her tongue. The way her little tongue moved on his cockhead was like nothing he had felt before. He had had a couple blowjobs before in college, but this, this was something else. He felt that It was as amazing as it was taboo, the girl was a natural. 

He didn’t try to get her to take him any deeper, with how small she was that could be dangerous, but once his orgasm was building and about to come, he had to restrain himself to avoid pushing his dick into her throat. 

Bonnie was a curious kid with a thirst for learning she knew how to pay attention. So once Andy’s moans and groans became louder and louder, she knew that his milk was about to come. And with one last long lick and a suckle, it came, he came loads, and held her head in place so it all ended up in her mouth, any other girl would have complained but she took it like champ, only looking up when he was done cumming to let him know to let her head go. 

Once freed, she swallowed everything in one long glup. His “milk” was just as tasty as it was the day prior, but this time it had a distinctive tinge that she recognized as her body’s own taste. She loved everything about the liquid she drank, and she let Andy know that, when with a smile, she looked up and asked “Can I have more later?” 

The boy couldn’t resist lifting her up, hugging her and giving her a kiss as deep and passionate as the one he gave her an hour prior. He was going to love the fuck out of her and enjoy this as much as he could. 

  
And he tried his best to do just that. Kissing her whenever possible, jilling her off after she did a good job with her homework, eating her out during playtime. And boy, did the girl love blowjobs, giving him seven through the day. They were barely apart through the it, hell it was a miracle that they weren’t fucking again during lunch. 

But they were during tv time. Once he put on another episode of Buzzlight Year of Star Command, she sat down on his lap. And once his body had the natural reaction to seeing Mira Nova on screen, he aligned Bonnie well on top of his cock and let her sit down at her own pace. It wasn’t long before her moans were overtaking the sounds from the TV, it wasn’t as if he was paying attention to them either, his body could barely focus on anything that wasn’t Bonnie’s unreal tightness. 

Still not even he was out of it enough to ignore a loud ass phone ring. One of the things that Mrs. Anderson had told him before leaving was that she would call him when it was time for her to go back home. So he was quick to tell Bonnie to pipe down as he took the phone and said “Hello?” 

“Hi Andy?” Said the familiar voice of Mrs. Anderson, “Is Bonnie giving you any trouble?” 

“Not at all” He said, realizing that even though he had stopped pumping, Bonnie kept lifting herself up and bringing herself down on his member, so fascinated by the sensation that she didn’t care that Andy was talking to her mom on the phone, still, she was an obedient girl so she covered her mouth to avoid making any noise. “We hit it off pretty well, she hasn’t left my side ever since I got here. You could say that she has been stuck to my body this whole time” 

Bonnie’s mom giglged at the other end of the line, before cutting to the point “Listen Andy, this is just a heads up, i’m already back in the state. I’ll be back home in a couple of hours. I’m bringing food so you don’t need to make dinner. Just, have everything clean and ready when I get there”

Bonnie, not knowing or caring that her mom was on the phone, tightened even more after impaling herself on his dick, making Andy groan right into the phone. “Are you okay, you sound in pain”

“No no, its nothing like that” he did his best to keep his voice stoic as he held bonnie’s waist with one hand a pushed himself back in making her moan.

“What was that?” Asked Mrs. Anderson “Is Bonnie okay?” 

“Yeah yeah, she just stepped on a lego. I’ll have her clean everything up before you get here” 

Without much more to talk, Mrs. Anderson ended the call after exchanging a few pleasantries, Andy put the phone down, and proceeded to make Bonnie experience the first (and hopefully not last) hard fucking of her life. It was as much of a reward for exciting him so much as it was a punishment for making her mom suspicious. But boy it didn’t sound like she took it as a punishment, cumming multiple times before Andy could feel her little womb with cum again. Once he did it both of them spent multiple minutes just resting on the couch before he made her stand and very sternly told her

“Your mom is coming home soon, pick up your toys… and clean up your stains” he said, pointing at the cum on the leather sofa, and the one in the ground coming out of her. “Once you’re done, come join me in the shower”

Excitedly, she did as he said, although this time, the shower they took was less fun and more focused on just cleaning themselves. When she asked why, Andy told her that it was because her mom was coming home, and it was very important that she didn’t know that any of this happened. When they got out of the shower, he made her pinkie promise that she wasn’t going to tell her mom about anything they did and promised to take her out for ice cream before she came home. 

  
And after they got everything cleaned up, and her legos organized, and everything as unstained by cum as it was when he got there, he dressed her up and did just that. He took her downtown for ice cream, and as they enjoyed their milky treats, she asked him about college and how it was to live in another state and she looked impressed and overjoyed as he told her about the most normal or banal of things.

Now that he had all that post nut clarity, he was once again stranged by how he could have such an innocent and casual conversation with a girl that he just spent the best part of a day and a half fucking into silly putty. 

The convo continued as they went back to the Anderson household, where they were greeted by Bonnie’s mom, “Oh Andy!” she said, disappointed somehow. “I told you I was bringing food” 

His stress went up and down after he said his name, he expected her to have found out about what they did, but he relaxed once she made clear that it was about the ice cream.”Oh, ma’am i just wanted to give her a last treat before i have to go back home and you know, to school” 

She gave him a defeated smile, before she invited him to take a seat… so he could eat takeout with them. And he did, he had a nice casual meal with them, before going back home. Eventually the day ended, and the next morninig he went back to college. 

Initially, school life hadn’t changed that much, it was boring and loud and obnoxiously scheduled. But that all changed a week later, when he got a nock on his door at the dorms. Once he oppened it, he was greeted by the friendly smiling face of Mrs, Anderson’s round, lovable face.

“Oh. hello” He said, nervously, he knew that there was only one reason why she would even be there, so he had all the reasons in the world to be afraid. “What are you doing here?”

“I wanted to surprise you” She said ending it with a smile. 

“With what?” 

“Well, firstly, by letting you know that we are neighbors!” 

“What?” 

“Yes, we moved to just around the corner a couple of days ago” 

“Oh. Thats… thats great” 

“Are you alone?” 

“Eh, no” 

“Then come with me!” She said, grabbing his hand and practically pulling him out

  
He closed his door with a key, before nervously following her. He asked “What do you need me for now Mrs. Anderson?” 

“Oh, nothing much, I wanted to offer you a place to stay with me and Bonnie”

“Thats, thats great” he said, nervously, before making an awkward pause before asking “Wait, just you two?” 

“yeah, didn’t you know? I moved out here because I got divorced”

With a single, lone “oh”, he ended the conversation, not knowing how to continue without making it awkward. He followed her until he was at her front door, and then, when he got in, he asked. “Say, why didn’t you offer me to stay back at the dorm?” 

“Because we need to talk about some things first” she said, somehow managing to sound matter-of-factly and excited at the same time.

“Things? What kind of things?” he asked. 

After the loudest lock announced with a click that the door was closed, Mrs. Anderson, told him in her best monotone voice “Simple things, like cartoons, and condensed milk”


	2. Babysitting With Her Mom

**Notes for the Chapter:**

> I have to admit, the making of this story was a bit hard for me because of things that happened to me, but I had to honor what the requester wanted. A huge thank you to all the friends that helped me finish and edit it, you all had great ideas.

“...Simple things, like cartoons, and condensed milk...” In Andy’s mind the words felt heavy like a sack of bricks, there was a knowing weight behind them. 

Trying to not show the sheer amount of panic he was in at the time, Andy simply followed her in silence once she started moving. He paid attention to the layout of the apartment memorizing it just in case he needed to run away in a few minutes. This new place was way different than her old house. It was way less fancy, even though most of the same stuff was around.

He didn't know why, but even though the place was big, it felt really cramped. Maybe it was the fact that this woman was probably about to kill him or send him to jail but his eyes couldn't focus on anything at all. 

When they got to the living room, Ms Anderson told him to sit on the couch. He really didn’t want to be here now, not at all, but without options or excuses, he just did as she said, swallowed hard, and waited for his doom. 

A doom that never actually came. Ms Anderson just left, his mind raced to tell him to run, that she was going to come back with a gun or a police officer or Chris Hansen. He wanted to get away but he was paralized by fear, and he was so for long enough for her to come back. He had no words that could describe his surprise when she entered the room carrying a tray with coffee and some cookies. The word “Unexpected” isn’t enough to describe how he felt at the time. And every second after that just weirded him out more and more.

She put them on the coffee table in front of Andy and sat on the sofa seat in front of him. Even though it only lasted for a few seconds, the silence that followed was the heaviest that he had ever felt, and she noticed. He was about to speak when she broke the silence ahead of him.

“So, Andy, before you say anything,” She spoke in what Andy could tell was a forced monotone “There are three things you have to know.” 

“What… what would those be Ms. A--” 

“Well, first of all. Stop calling me Ms Anderson.” She said, showing the first hint of emotion he had seen from her ever since he came through the door, and that emotion was annoyment “My name is Shirley and I would be happier if you called me that. You would make this feel less weird.”

_ You think YOU feel weird _ , Andy thought, he couldn’t feel any weirder himself but he knew he couldn’t be silent for too long, so he responded with “Okay, I will Ms. A- Shirley. Sorry, it's just, I’ve known you since I was a toddler, it's going to take some getting used to.”

“Don’t worry, I’m sure we’ll have plenty of time to get to know each other better.” 

“Oh?” 

“Because of thing two, you see?” 

“And… what would that be?” 

“I know what you did during that weekend.” 

  
  


Sheer fucking horror was written all over Andy’s face, his life was over, he would be dead or jailed or dead in jail. Yeah, probably that one. Well, that would be if Shirley didn’t continue before he could completely break down and overthunk himself to death. “And thing three... I’m not actually mad about it.”

It was as if Andy’s brain had bluescreened. He somewhat couldn’t process what she said for a whole minute. After which he spoke only to say “Excuse me, can you say that again?”

“I am not angry with you for what you did.” 

He still couldn't understand. And she could tell, to help it, she pulled out her phone, quickly navigated to the video section and pressed on a particular one. The very recognizable sounds of a very familiar scene that Andy would never be able to forget started playing. He thought "no way" until Shirley put the phone on the table, facing his direction. 

It was a video of him fucking Bonnie on Shirley's bed, recorded from one of the upper corners of the room. Shirley instructed him to press the skip button to go to the next video, after doing so, a video of him and Bonnie taking a shower started, while it was innocuous at the start, he knew that it ended up with him jilling her off. The next video she told him to put on had him and and Bonnie walking around the house completely bottomless and the one after that had him fucking the girl while talking to her mom on the phone. 

Shirley knew everything, she had proof of everything, and yet… she was not mad? "How? Why? How come you're not mad?"

"I'll answer in order: first, I had secret cameras all over the house, second, I'm a very serious voyeur, and last… because I've never been this horny about anything in my entire life before."

"Horny?"

"Do young people these days not say horny? It means I'm wet, excited, aroused, take your pic, I have more."

"But you're her mom!"

"And you're the boy who fucked her. Andrew, if I was mad at you for it, you would be in jail already getting butt fucked by bubba, but I'm not… I actually want you to do it again."

"Do it again?"

"I knew that gen z was dumb, but this special. It can't possibly be that hard to grasp: I want you to put your penis in my daughter again, though this time, I want it to happen while I'm watching."

"And then you'll let me go?"

"You're not trapped here, you can go now and never come back if you want. These videos will be enough for me to jill off until Bonnie goes to college I'm sure."

"Then what's the catch?"

"There is none, Andy this is not extortion, this is a friendly request."

It took a while to process, during which Shirley took a cup of coffee from the tray and a few cookies, she drank and ate while Andy went through the five steps of a crisis of self all in 15 minutes. After which, he said “Will it be right now? Is she here?” 

“No, she’s at school. And she’ll be tired when she gets here. So i’ll tell you what, go to your dorm, think about it and come back on friday. If you say yes, I’ll let you stay here, you won't have to pay any rent”

“O-Okay,” he said.

The sheer casualty of their conversation, and how much her tone had softened ever since she started talking wrecked his brain. And it just didn’t stop. As when he was getting up she spoke in the sweetest tone, the same she always talked to him with when he was a little boy. She said “Take a few cookies with you, eat something sweet, you totally need the sugar. You’re pale as a paper sheet.” with such a sense of unbound honesty and innocence that she sounded like someone who didn’t just tell him that she wanted to see him stick his dick in her daugher. 

He nodded and took half of the ones she had in the tray, put them in his letterman jacket and exited the apartment, surprisingly for him at least, as he went out, it didn’t feel as small as before. It wasn’t as cluttered as he thought it was. It was probably a nice place to live in. 

What followed was the weirdest three days ever. During the day they were normal, or as normal as they could be with him being more distracted than usual. But in the afternoon, outside of class, he got, silent, pensive. Spent the rest of the day thinking about it in his room. Come friday, he had to make a choice. 

She could have him by the balls if she really wanted to, yet she gave him an option, this was the train of thought with which he justified to himself going back there. After his classes were over on friday, he took a backpack with a change of clothes and he went back to Shirley Anderson’s apartment. 

After she opened the door, Shirley looked genuinely surprised to see him there. She let him in and told him to put his backpack anywhere, that she still hadn't finished unpacking their stuff. There was clutter everywhere so a little bit more mess wasn’t really going to make that much of a difference. 

He sat down on the sofa, and waited, by how the place smelled, he deduced that Ms Anderson was preparing food. He was right, as she invited him to eat with her and Bonnie. Bonnie herself ran to hug him when she saw him, and he hugged her back. They ate together in the circular table that Ms Anderson had in the Kitchen. Admittedly, the day they had leading up to the night was remarkably mundane, disturbingly normal. 

That normality ended however, when night fell. Shirley informed that it was time. He soberly nodded as he still wasn’t sure if she was serious. He asked to take a shower first, and she told him to go ahead. In it, he pondered again, thought himself into a circle one more time, thinking that the second he got out of the shower she would be holding a gun at him or a police officer, that this was just a long ruse. But when he actually did, she was waiting by the bathroom door, with more comfortable clothes, and a very excited smile on her face. 

He had dried himself before coming out, but he felt his forehead getting damp, as if the place was hotter than a summer day in the desert, even though the apartment was well refrigerated by an AC. As earnest as it was, there was something in that smile that made him nervous.

“Why are you wearing that?” Shirley asked.

“Wearing what?” It was an honest question. Her answer was just pointing down at his waist, so he said “I was in the shower, I’m supposed to wear this.” 

“Why? You’re already dry and we are going directly to the room to do the nasty,” Anderson said jovially yet matter-of-factly “Bonnie has already seen it and I'm about to see it too. So why bother?” 

Seeing no point in having an argument, Andy instantly conceded, and dropped his towel, letting the woman see his body in all of it’s barely legal glory. 

Shirley whistled after seeing what he was packing “You certainly weren't using the cold water…", he blushed at the compliment but didn’t cover himself, instead he followed towards Bonnie’s room, where Bonnie was already naked on the bed, impatiently waiting for them. 

Andy asked Shirley if she was going to record this. She answered with “No, I'm just going to sit and watch. Now c'mon go ahead, you know what to do, you did it before”.

  
  


He still felt weird, it was the first time that he was consciously going to fuck someone with an audience, but he tried to push his concerns out of his mind, for a minute, he got on the bed and greeted Bonnie again. She was happy to see him, and even more to see his dick again. She gave him a hug, and he kissed her forehead, before giving one last look back at Shirley, who gave him two thumbs up and a smile.

With one last confirmation of her mother’s approval, he kissed Bonnie on the forehead again, before getting down and kissing her on the lips, then the chest, then her belly, and then her mound. Bonnie moaned, and her mother licker her lips, this was so much hotter in person.

When she was wet enough, he decided to stop delaying the inevitable, lined himself up and pushed manhood in her. It had been a while since they last did it, so he gave it a minute before he started moving, but when he did the young body swayed back and forth as she panted and moaned while Andy shoved his cock into her over and over again. 

As a mother Shirley should have been disgusted, horrified, and above all wanting to kill the man that took her daughters innocence from her. But in the moment, she reached her hands down, unbuttoned her jeans, slipped her hands past her waistband, and began to feel her pussy get wetter as she watched the scene unfold before her. 

She felt her slit already getting moist as she witnessed Bonnie’s prepubescent body be dominated. She didn't expect to get so wet so soon, but she didn’t care. Maybe it was because her husband didn’t satisfy her before the divorce and so she was aching for any type of sex, or maybe she was more depraved than she thought and always wanted to see this kind of action go down. 

Whatever her reasoning was, she needed to see more. Deep down she wished she could have seen it in person from the beginning, to see just how Andy got Bonnie wet enough to take his big cock in her tiny pussy, but if everything played out as she hoped it did, she would soon find out and then some. 

For now though, she continued to enjoy the show. Her fingers danced around her clit and slit as she altered her movements to how intense the two were going. Andy would alternate it seemed as he would have short bursts of quick thrusts between long, but powerful, thrusts every so often. Ms. Anderson eventually snuck her fingers inside of her, feeling herself deeper and deeper relishing on how wet she really gotten from her own ministrations. 

She tried her best to keep mimicking them but she knew that without a toy she wasn't going to be able to copy them exactly. So she settled for her fingers and tried her best to make sure to match them, even though her pussy ached to go to town on her now. 

For the next few minutes her world was filled with a euphoria as the thrilling feeling of breaking a taboo filled every part of her being. She was getting close, but she didn't want to finish too soon as she had hoped for her body to finish in time with them. Luckily her prayers were answered as she heard Andy say that he was going to cum. 

Shirley Anderson watched with greater intent as she was about to witness her Andy about to cum with her baby girl. Her mind raced with thoughts of how he was going to do it. Was he going to just pull out and cum on her belly? Maybe turn her around and do it on her back and ass? Perhaps he was going to go full porn star and position her and do it on her face. Or was he going to…

No… he was too much of a gentleman, he would never…

As soon as she thought that though, Ms. Anderson watched as she saw Andy grunt and moan while keeping his dick firmly in place within Bonnie’s pussy. He breathed heavily as Bonnie cood and moaned while her pussy was being filled. She couldn't believe it. Bonnie was getting a creampie, and unless her eyes weren’t working right and she was mistaken, the young girl was loving it. 

After what felt like forever, Andy withdrew his cock from her daughter’s pussy as a large glob of cum fell from her pussy. Andy let her enjoy her blis for a few minutes, but eventually he patted her on the chest a couple of times and she turned her face to look at him. He moved towards her, letting his cock hang, throbbing inches away from her cute and innocent face. Without any prompting, Bonnie opened her mouth and began to lick and suck on his cock, cleaning up his cum mixed with her juices. 

Ms. Anderson felt herself tingling all over with anticipation. She hadn’t quite gotten herself off yet, but she was definitely going to get hers soon enough. She watched as Andy took a towel nearby and began wiping down Bonnie’s body with it, cleaning all the cum and sweat that had accumulated from their session. Andy got the young girl’s pajamas and dressed her before tucking her into bed. With a long and passionate kiss goodnight, Bonnie was out like a light as Andy began to exit the room. He stepped out of the room and closed the door behind him. With a sigh, Andy relaxed after having done well at putting bonnie to bed. 

It was as if he was tranced for a bit, having completely forgotten that he was putting on a show for someone, clearing her throat, Ms. Anderson made her presence known. Which was followed with a comment on how it is such a joy that he had found a way to get Bonnie to sleep peacefully and without prottest. 

Naturally Andy was startled at first but didn't yelp as he stifled himself not wanting to wake Bonnie. Whispering, he asked “What next? Will you send me home?” 

  
  


Instead of doing that, Shirley took Andy by the hand and led him down the hall to her bedroom. There, the middle aged mother turned around and brought Andy in for a passionate and forceful kiss. Needless to say the young man was caught off guard, but that didn't stop him from returning the kiss with the same intensity when he got his bearings. 

The two’s hands flew up and down each other's bodies, eventually resting on Andy’s crotch and Ms. Anderson’s ass. When the two were thoroughly warmed up, Ms. Anderson made the next move as she dropped to her knees, took his cock and gazed upon it as it twitched inches from her face. The smell of it filled her nostrils and she knew where it had just been, so the scent of her daughter’s cunt was as fresh as it could ever be. The aroma of the juices that had coated it before still fresh as the one who helped make the smell of pure and unabashedly sinful sex was sleeping in her bed only a few doors away. 

Not wanting to waste anymore time she opened wide and took his cock in her mouth with a vicious hunger. After the appetizer she had witnessed earlier she was more than hungry, she was starving for affection and this boy was going to fill her until she was satisfied. Her head bobbed back and forth as if her body was moving of its own volition. She had no self control as she choked on Andy’s cock, wanting to take it as deeply as possible. The taste of it overpowered her senses as the flavor of his cock and her daughter's pussy graced her taste buds. Her mind was foggy with the taboo tastes of a boy she had known since he was a child and her own flesh and blood that he had just fucked. 

Unable to take it anymore, she popped Andy’s cock out of her mouth and stood up. Hastily she dropped her pants to the floor and removed her shirt. Grabbing Andy by his shoulders she moved him over to the bed and forcefully pushed him down onto the mattress. He laid there stunned for a second, which was enough for Ms. Anderson to mount him and slip his cock into her wet pussy.

It went in smoothly, her sheer wetness allowed there to be little to no resistance as the boy’s cock penetrated her. She felt absolute ecstasy in that moment as Ms. Anderson felt a cock inside her after so long. It was so big, much bigger than her ex husbands, and much more lively. The essence of youth was very abundant as his cock throbbed and pulsed inside of her. Even though he had just gotten off it was like he hadn’t had sex in a week with it felt with this well experienced lady. 

Ms. Anderson having savored the initial shock of being penetrated began to move her hips. She grinded her hips as she felt his fat dick move stir up her insides. It reached and pressed against her in ways that she had only felt back when she was a teenager. Leaning down, she locked lips with the young man again. Her tongue probed his mouth and danced with his tongue. She remembered that he had used this tongue on her daughter before much like how he used his dick on her. The memory of that fueled Ms. Anderson as she began to bounce up and down on Andy’s dick. Her most sensitive spots felt his dick press against them again and again as she wanted to get off as soon as possible.

Finally, after riding on his cock, Ms. Anderson felt his hot spunk burst forth and filled her. She never felt a load so thick before, nor in this quantity. It felt like he was going to cum non stop. That thought set her over the edge as she kissed him to silence her orgasm. Her pussy clenched around him as if it was trying to squeeze every last drop out of him to ensure she was filled. Soon, the pulsing sensation stopped. Ms. Anderson stayed on top of Andy for a little while longer as she felt him inside her. She almost felt like she could feel his heartbeat through his dick still inside her. 

Ms. Anderson rolled off of Andy and onto her bed. The two panted heavily, trying to catch their breath from the amazing sex they just had. Andy was still in shock as the sex with her was so intense that he thought he was going to die. The only word that could realistically come out of his mouth was “wow”. 

“I know right?” Shirley said in honest bliss “Best sex I’ve had ever since the divorce.” 

“You’re divorced?” 

“Yes, it’s part of the reason we moved here, that whole ‘new place, new life’ kind of vibe.” 

“I wouldn’t know it, I live in a dorm.”

“No you don’t,” Shirley said, as she rolled over to open her night stand’s drawer, after going around it with her hand for a bit, she pulled out a key, complete with a keyring and everything.”It’s a copy of my key.” 

“You sure about this?” 

“Sure, I was being serious when I told you i was going to let you live here if you wanted to.” 

  
“I don’t know though, my friends already got used to me, and we split the rent. I couldn’t just leave them with such a load just like that before the semester ends...”

Shirley sounded pensive for a second before saying “Take the key anyways, you’re free to come and go as you please. Doesn’t matter why. Come if you want somewhere to rest, or a meal, or if you want to do Bonnie… Or me.” 

“Wow you’re pretty serious about this aren’t you?” Andy said, finally realizing what Shirley Anderson had been straight up telling him for so long. 

“Just promise me something.” 

“What’s that?” 

“That you will consider moving here when the semester is over, it’s been so long since I lived with a man.” Shirley made a pause, and chortled a bit before saying “Oh, look at me. I did it with you once and I’m already getting attached!” 

Andy smiled, fully understanding how she felt now, he said “I promise. I’ll come here often, for Bonnie, and for You.”

Shirley smiled. “And here I thought that the first thing in a college student’s mind would be the free food.” 

Both of them laughed their asses off, before exhaustion caught up with them and sent them to sleep. When morning came, Andy woke up beside Ms. Anderson, and saw that none of this had been a dream. And it was then that he thought to himself… “This is going to be an Interesting couple of months.”

He didn’t know how right he was. 

On some days, nothing happened, in others he only came for a meal before a busy day. In others, he got his world rocked in ways he couldn’t have expected. Like when Ms Anderson sat on the couch along with Bonnie and Andy. Even though she stopped going out on dates and stayed home more often, she still had Andy come over to help with some minor chores around the house and because Bonnie got fairly attached to him as others saw it. They made it work as Bonnie enjoyed the attention, Ms. Anderson got a reliable man around the house and Andy made a little money here and there and had good company on the weekends. 

That evening, the three of them watched one of the latest family films that topped the box offices upon release. They watch together, cuddling up on the couch. Although it seemed that Bonnie was squirming a bit in place as she fidgeted and moved in what seemed like discomfort. Ms. Anderson however aside from a little heavier breathing, was doing fine. Andy, however, sat there, as he fiddled with two devices in his hands. Two remotes to be exact that had dials that slid up and down and controlled the vibrators that were placed inside the mother and daughter duo.

Since the movie started, Ms Anderson made a game up that whoever could last the longest into the movie before asking for sex could do it with Andy first and get all the creampies. Bonnie thought it sounded fun as she was told it also meant she could play with some new toys that momma bought for them. Bonnie knew that when it came to Andy and toys, he was the best and had the most fun with her. She accepted, however it was a challenge for the little girl to keep herself contained through the onslaught of pleasure that Andy doled out while controlling her virbrator. He was going lightly on her to be honest. Meanwhile Ms Anderson was being given a greater challenge as Andy didn't go easy on her, as requested. He could feel it in their grips as Bonnie clung to his shirt and Ms Anderson gripped his hand within hers. Both ladies wanted Andy so badly they endured. 

However, by the third musical number of the movie, Bonnie broke, screaming out how she needed andy to fuck her. In her heated words she didn't realize that she was ultimately giving up and forfeited the competition. Andy turned off the toys for both ladies and they proceeded to remove them. Just as the bet stated, andy was going to fuck Ms Anderson first. However, as a good mother she wasn't going to let her daughter out of the fun. She laid back on the couch and told bonnie to come up and straddle her face like a pony. Her eyes gleamed with the idea of how fun that sounded and jumped right up to ride her moms face. Andy on the other hand wasted no time getting his pants off and ready to fuck as he was hard from having gotten to control two women and how much pleasure they received for the last fourty minutes. 

Lining his dick up with the mom's pussy, he thrusted forward eliciting a moan from Ms Anderson. He thrusted into her and began to fuck her pussy that he warmed up earlier. As he thrusted, he watched the loving sight of Bonnie being eaten out by her mother. Ms Anderson lapped and licked at herbdaughters pussy as she felt Andy’s dick fill her. The three kept at it for a time until Andy began to quicken his pace ready to fill Ms Anderson’s pussy.

Driving it all the way to the base, Andy's cock pulsed as he shot ropes of white hot cum in the mother, as she continued to eat out her daughter. After a few moments to come down from his orgasm, he withdrew himself from her as his cum seeped from her pussy. Cock still hard he took Bonnie around the waist and lifted her from her mother's face. Now that she was nice and warmed up from the toy and her mother, Bonnie slid down on Andy's still hard cock. 

Their bodies rocked with one another as he thrusted into the girl he kept aloft in her arms. Ms Anderson watched as her daughter took his dick, crying out in pleasure. It was a wonderful sight to behold as she reached down and kept rubbing her cream filled pussy. 

Andy felt another orgasm build as she withdrew himself from the young girl but kept her close to his body. He was just in time as he stuck the tip back into ms Anderson as he let another load fill her up and seep out again. Bonnie began to pout as she saw what was supposed to be her own cum. 

They compromised and agreed that Bonnie would go another round with Andy while she ate out her mom and reclaim her cum. They spent the rest of the movie fucking and cumming while the colorful and family friendly film played in the background. 

And that was just one of the least wild days that he spent on that house. Nowadays he could remember a particular Friday in which Ms Anderson, Bonnie, and Andy sat and ate dinner together that night. Andy came over to look after Bonnie while Ms Anderson ran some important errands that she couldn't take her daughter to do. They spent the day playing games and having fun by the time Ms Anderson came home she had insisted Andy stay and have dinner with them. He felt it would be rude to deny such a generous offer. 

He continued to play with Bonnie while Ms Anderson made dinner for them. It was a rather simple meal of chicken, macaroni and cheese, and peas. Despite its simplicity, it was still leagues better than dried noodles or the food that the cafeteria served him. As they ate happily together, Bonnie being a typical child resisted eating her vegetables. Ms Anderson scolded her child and told her that if she didn't finish her veggies she wouldn't have any dessert. 

The young girl's mood changed in an instant. She mixed the vegetables up with the mac and cheese and ate it fast as if she was able to speed eat past the flavor. It looked like she had more intent than normal than just a regular dessert would have. Whatever it was, Andy looked forward to it too. 

They all finished their meal and were satisfied. Andy took care of the plates and took them to the kitchen. Ms Anderson called out to Andy and asked him to get some dessert stuff like chocolate syrup and whip cream. He was a little confused as to why just those items. But he was sure there was a good reason. 

Walking back with the sweet toppings in hand, he was met with a sight that pieces everything together. Bonnie and her mom were both completely naked. The young girl was situated atop the table while the mother was sitting in a chair patiently. Andy took the hint and removed his clothes. While he was undressing, Ms Anderson grabbed the chocolate to drizzle onto Bonnie and sprayed whip cream onto her nipples and pussy. Bonnie giggled as she felt the cool confectionary treats fall on her skin and anticipated what fun they were going to have. 

As Bonnie laid on the table Andy and her mother towered over her with hungry eyes, licking their lips. They set in on the girls sweet body, licking and lapping at her skin and removing the sweets. They made quick work of her and now were just enjoying her body naturally. Ms Anderson kissed and sucked at Bonnie's neck and ear, while Andy set out to devour her pussy. The two worked in tandem getting her off in a matter of minutes. 

Next was Ms Anderson who was given the same treatment, except in her case it took much more chocolate and whip cream to cover her more sensitive spots. Andy and Bonnie both started at her breasts, suckling on her as if they were both babies looking to feed. She thought it was adorable the way they sucked and licked at her nipples. Andy proceeded to go lower on Ms. Anderson while Bonnie went higher, kissing her neck and lips. Ms. Anderson would have to thank ANdy for teaching her daughter so well. 

She was soon lost to the sensation of Andy eating her pussy and Bonnie running her tongue all over to take up the sweets that they had drizzled on her earlier. They worked in tandem getting Ms Anderson to her orgasm quite quickly. In the midst of her orgasmic pleasure she managed to reach her hand between her daughter’s legs to finger her, while her other hand was placed firmly on Andy’s head and laced her fingers through his hair. She clenched up when the sweet release the two gave her washed over her. 

Andy stood up and wiped his mouth of the pussy juices he was just drinking up. His cock stood hard and rigid, raring to go. The mother daughter duo decided to help themselves to dessert as they covered the young man’s cock in the creamy and chocolaty toppings. Bonnie licked up all of the sweets, reveling in the flavor of her babysitter and how he mixed with the sweets. When he was cleaned up of all the cream, Ms. Anderson took his shaft into her mouth and enjoyed the remnant flavors left behind on him. The ambitious mother kept going ferociously as she seemed the most hungry for Andy’s own personal cream. She was rewarded thusly as he came in her mouth. 

Ms. Anderson swished and savored the flavors of his cum in her mouth before taking her daughter and kissing her. She pushed the contents of her mouth into hers and mixed it between them with their tongues. Andy watched as they made out and hummed with pleasure as they slowly drank down his cum.

  
  


Bath time was kind of a no brainer after such a messy dessert. The three of them stood in the master bathroom’s shower, which was large enough to accommodate them all comfortably. The water came down upon them washing away the stickiness that they had enjoyed cleaning up with their tongues. But now they needed to clean it off properly. Andy and Ms. Anderson both washed off Bonnie’s body, who giggled as they tickled her in a few spots during the process. The two adults also enjoyed a little attention with each other as they washed and scrubbed one another down, especially in the hard to reach places. 

Once they were thoroughly cleaned though, they did not stop the shower. They continued to enjoy the warm water as it washed over them and relaxed their bodies. The scrubbing and touching had an added affect to them as they became aroused from the attention and affection. Andy was particularly noticeable as his cock throbbed and pulsed. Bonnie was at the perfect level to enjoy it as she reached up and stroked it. Meanwhile, Andy and Ms. Anderson kissed each other passionately, all the while Andy reached down and fingered the sopping wet milf pussy. 

The three worked on one another with vigor. Bonnie continued to suck and lick on Andy’s balls while stroking him, all the while he added on kissing and licking to the attention he was giving her mom. Soon though they were ready to move onto the next phase as she bent over against the wall and presented her pussy to the young man. Andy moved himself to a better position, causing Bonnie to move slightly to allow him to fuck her mom. That didn’t stop the young girl though as she merely repositioned herself to be right where the action was. 

Andy thrusted into the milfs pussy. She moaned as his shaft went in inch by inch before it bottomed out in her. Meanwhile, Bonnie watched as her mother was fucked by her babysitter, his cock thrusting in and out with the sound of their schlicking cutting through the water splashing them. Ever an eager little girl she stuck her tongue out and began to lick along where her mother's pussy met Andy's dick. 

The three kept at it for a good while. Ms Anderson especially loved the attention as her daughter licked her clit while a young man was loving her so passionately. She couldn't believe she could be so lucky. The attention was too much as her body gave in and came, clenching around his shaft tightly which caused him to cum from the added sensation. 

As he pumped ms Anderson full of cum, Bonnie kept licking them, the sensation sending shivers throughout their bodies. She was rewarded for her hard work as his cum seemed out a bit from the mother's slit once he removed himself. She drank up the mixture the two had made as if she was told it was going to make her big and strong. 

When she was finished licking away what had spilled from her mother, she looked and saw Andy's member in front of her face. Instinctively she opened her mouth and latched onto it, sucking on it and trying to get more of his cum out of him. He caressed her head and gave gentle thrusts as he tried to help facilitate her efforts and tried to give her a reward for being such a good helper. 

  
  
  


As time went by, his attitudes with them became looser, wilder, and even he had to admit that they had become more perverted. A good example of that was, well, tea parties. Tea parties were a normal part of play time for any little girl at Bonnie's age. However, after everything they went through, Andy knew that their tea time would be a little more special. And with her mom joining their fun it was all the more fun. Along with the three of them the other guests at their tea party were some of her toys, set up and sitting in the spots between them. Andy did have to admit that it was a tad awkward to have himself getting sucked off in front of his old toys he had given her.

Then again it was weird that he was fucking a little girl and her mom, but that wasn't going to stop him. Especially since they were so skilled at sucking him off. The two this time were working together to make some fresh "cream" for them and their guests. Bonnie would suck on him for a bit only to trade off and let her mother have a go. 

Andy watched and enjoyed how they had such enjoyment in sharing him. It was as if their mother and daughter bond was strong enough to know how to work with one another to make him feel the best. Their tongues caressed and licked his cock in just the right ways that he felt his orgasm hit quicker than expected. He came without warning, firing the first shot between them trading off and let one fly. The two positioned themselves with their mouths wide open looking to catch the cream to go with their tea.

After Andy was finishing giving out his thick creamy goodness, the ladies took their plastic little tea cups and let the cum drip from their mouths into them. It only filled up the cup a quarter of the way each but it was still enough to cream their "tea" to satisfaction. 

They looked to see where the first shot of cum had landed and saw as Jessie the cowgirl was lucky enough to get the first bit of cream. They shared a laugh as they continued their party. They drank their tea and moved to the bed where they wanted a little extra cream. All the while Jessie sat in her chair as she let the cum of her previous kid sit on her face and witnessed him fucking his new kid with her mom. 

The months went by, and as they did he got more and more open, and a hell of a lot more depraved. Sometimes he went there just because he wanted to wet his noodle, sometimes however, he got called there by Shirley to take care of Bonnie while she did something else. 

He had gotten used to hanging around her, even when nothing nasty was happening she was a joy to hang around with, so whenever Shiley asked him to babysit, he gladly did. Though... Play time was always Andy’s favorite part of babysitting Bonnie. Having time to indulge in a little imagination and make believe took him down memory lane and reminded him of when he would take his toys and set up elaborate and imaginative scenarios. He would still play with her and her toys, but this time was a little more of a mature game. Especially with Ms. Anderson involved in their little game of dress up and make believe. This time, taking a little inspiration from one of Andy and Bonnies favorite toys, Woody and Jessie, they decided to be a cowboy and girl tussling with a cow that was acting up a bit. And it was up to them to calm her down. 

Andy dressed up with a cowboy hat and a vest with a little star badge on the right side, Bonnie practically was in the same thing as she rode on her mom’s back, who was wearing a headband with cow ears on it and a shirt with cow print on it and a tail. 

However that was all they were wearing. None of them wore pants as they were roleplaying the cowboy scenario. Ms. Anderson was on all fours as Andy was positioned her behind her, driving his hips forward causing her to shift back and forth as he played with the tail, which was a set of anal beads that fit in her ass. Every once in a while Andy would smack her ass leaving a red handprint on her as if he was branding her. All the while Bonnie sat on her back, toy inside her young pussy as the movement shifted it inside her giving her pleasure. She had in her hands wrapped around reigns that led to a gag that Ms. Anderson was biting down on, muffling her moans of pleasure.

Yips and hollers could be heard dispersed between the sounds of moans and gasps of pleasure that the three were experiencing. Andy every so often would lean forward to kiss Bonnie on her back, neck, or lips, which when the girl leaned back would pull her mothers head back with the reigns. Andy quickened his thrusts as he caused the mother to rock back and forth more rapidly. Bonnie gave a yeeha as she rode her bucking mother. Andy came inside her which caused Ms. Anderson to give a loud, but muffled, moan. Andy pulled out, Ms. Anderson collapsed, and Bonnie dismounted her mother.

Letting the naughty cow rest, Andy pulled out the toy nestled between Bonnie's legs and laid her on the bed. He told her she was a good little cowgirl and deserved a big girl treat for staying on and helping calm the horny cow down. Andy slid his dick into the girl who let out a cry of pleasure. Gently he thrusted into her taking his time to loosen her up before going harder and faster with his thrusts. Her voice let out a high pitched squeal as she came from his dick pumping his cum deep into her. 

Andy breathed a good long sigh as he was pleased with a job well done taking care of his little ladies.

His little ladies, he had started calling them that (at least mentally, to himself) two months in, maybe he should have realized it then, but things had become much more than just sheer lust. He was happy here, in and out of bed. Whether it was in a flare of absurd lust or just spending a cozy night eating ice cream and listening to cheerful songs. 

Everything was changing, even the sex, there was less of it around the living room, the bathroom and Bonnie’s room, and there was way more in the master bedroom. The master bedroom of the house was a different experience to have sex in than in Bonnie’s bedroom. Instead of colorful furniture, decorations, sheets and toys that almost looked like they were judging you, there were solid colors, cohesive decorations and designs and overall had an air of maturity to them. Even though he was still fucking Bonnie with her mother watching, it was less of an awkward experience. 

That night, they decided to change it up and have a more vanilla night in Ms. Anderson’s room. No games, no elaborate situations, no odd positions. Just the three of them on the bed, making love. Bonnie rode atop of Andy, her hips grinding slowly into him as his dick penetrated her deeply and stirred her insides. Andy held onto her hips and helped guide her along through their shared pleasure. All the while Ms. Anderson watched on as her baby was riding the babysitter. Her fingers caressed her pussy slowly as she was turned on by the sight before her and wanted to enjoy the show a little more for herself. 

The show however was soon over as Andy grunted and came. Bonnie soon followed as his hot semen filled her. Her body went rigid as her orgasm washed over her. She collapsed against Andy's chest and the two shared a kiss. Andy’s dick slipped out of the young girl as the cum he had pumped her full of followed. They cuddled on the bed for a bit before Bonnie fell asleep peacefully from the warm and soothing nature of Andy and his heartbeat and breathing. Gently setting Bonnie off to the side and onto the bed, Andy shifted his attention to Ms. Anderson. 

The two kissed and caressed one another gently and lovingly. They were methodical and careful as to make every touch loving and feel good. Eventually, amidst the make out session, Andy was atop of Ms. Anderson and slipped inside of her. His tongue probed her mouth and danced with hers as he pumped himself in and out of the loving mother. She moaned and whimpered in pleasure as she felt his young cock fill her and penetrate to her deepest reaches. It was so nice to have a big strong man in her life. Andy may have been young, but he cared for both her and Bonnie greatly. Not just as a lover, but as a partner. 

He was kind, gentle, caring, firm with Bonnie when he had to be, but always took her feelings into account first and foremost. With her, he was considerate, listened to her, mature for his age as they talked about life and how things were going for both his schooling and her work. They connected on a level that was deeper than just sex.

Ms. Anderson wrapped her legs around Andy as he continued to hump her. She knew he wasn’t going to pull out, but she wanted to feel like she had him no matter what and was never going to let go of her man. She reached up and kissed him deeply as her arms wrapped around his back, feeling up his shoulders. Andy’s thrusts quickened as he approached another orgasm. She was also on the cusp of hers, yet she knew as soon as he spilled his seed in her, it would hit her as well. 

He had cum in her many times before, and she looked forward to many more times, but she was guaranteed to feel the absolute euphoria of being filled with Andy’s young, hot, virile cum. Her pussy clenched around his dick as if trying to milk him even more. Even though he had just unloaded and brought her to orgasm, Andy didn’t let up on his thrusting. Still hard, he kept going for another round as he knew a mother like her deserved another hearty dose of cum. 

Andy loved how her life was at this moment. He loved them, over time, he realized that he had caught feelings. He loved Shirley and he loved Bonnie, and he was grateful to know that they both loved him back. 

His life had gone pretty good, his grades in college were rising, he had found a good part time job, and life with his ladies was pretty amazing, since he began spending more and more time with them on the daily. So much so, that in a few months time, his friends in college had started to wonder what had happened to him, since he had completely disappeared from it. 

It wasn’t until one day out in the time, a few of those friends saw him going into a house, and after a few minutes they decided to go and knock on the door, pay their friend a visit, maybe even figure out why he left the dorms. And so they did, they knocked on the mahogany door, and a couple of minutes later, someone opened it. 

It was a woman, probably in her forties, with long brown hair, glasses, a face that made it obvious that she spent a lot of time smiling, and very, VERY pregnant. 

Weirded out that Andy was living with a pregnant woman, one of them said, “Eh.. Sorry for the intrusion, we’re Andy’s schoolmates. We wanted to ask him something, is he here?” 

Elated, she opened the door more, and let them in. “So, you’re the boys from the dorms that Andy has told me so much about.” 

One of them, kinda bitter, responded with “Well, he hasn’t told us much about you, are you like... his mom, or his landlord?” 

Shirley stopped and turned around and said “No nothing like that. I should probably present myself.” she showed them her right hand, so they could see the ring “I’m Shirley Davis, Andy’s wife.”


End file.
